Al Capone: Undone by a Tax Bill and an Untreated Disease

Al Capone ended his criminal career plucking a banjo in an Alcatraz prison band. This episode strips away the Scarface myth to follow the real chronology: a barber’s son born in Brooklyn in 1899, expelled at 14 for striking a teacher, schooled in extortion as a bouncer at Frankie Yale’s Harvard Inn, and slashed three times across the face by Frank Galluccio. He hated the nickname that followed, hid his left side from photographers, and asked his inner circle to call him Snorky instead.

Invited to Chicago by Johnny Torrio in 1919, Capone inherited the whole operation at 26 after Torrio was ambushed and retired. He ruled through dynamite and bought officials while courting the public with jazz patronage and a Depression soup kitchen. The St. Valentine’s Day Massacre shattered that image, and the federal government answered with accountants instead of bullets. Convicted of tax evasion in 1931, he was already carrying the untreated syphilis that would destroy his mind.

  • Capone gave $250,000 to the campaign of Mayor William Hale Thompson, and his men bombed polling places with hand grenades during the 1928 Pineapple Primary.
  • Rival Joe Aiello offered the chef at Capone’s favorite restaurant up to $35,000 to lace his soup with prussic acid. The chef confessed instead.
  • On February 14, 1929, gunmen dressed as police lined seven of Bugs Moran’s men against a garage wall and shot them, and the newspaper photos made Capone public enemy number one.
  • A 1927 Supreme Court ruling made illegal income taxable, and Capone’s own lawyer handed prosecutors a letter admitting income for 1928 and 1929, which Judge James Herbert Wilkerson admitted as a confession.
  • Paroled in 1939, Capone received penicillin in 1942, too late to reverse the damage. He died in 1947, while successor Frank Nitti kept the Chicago Outfit quiet and profitable.

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